1-methyl-6-(1-methyl-2,3-dihydro-1H-indol-3-ylmethyl)-1,2,3,6-tetrahydropyridin-3-ol | 484652-81-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 10,11-麦角林
• 英文名称: 1-methyl-6-(1-methyl-2,3-dihydro-1H-indol-3-ylmethyl)-1,2,3,6-tetrahydropyridin-3-ol
• 英文别名: 1-methyl-6-[(1-methyl-2,3-dihydroindol-3-yl)methyl]-3,6-dihydro-2H-pyridin-3-ol
• CAS: 484652-81-5
• 化学式: C₁₆H₂₂N₂O
• 分子量: 258.363
• InChiKey: FWRDHNJYGXWDCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.71
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methyl-6-(1-methyl-2,3-dihydro-1H-indol-3-ylmethyl)-1,2,3,6-tetrahydropyridin-3-ol 在 三氟甲磺酸 作用下， 反应 14.0h， 以42%的产率得到(5aS*,6aS*,10aR*)-4,7-dimethyl-4,5,5a,6,6a,7,8,10a-octahydroindolo[4,3-fg]quinoline
  参考文献：
  名称：

  Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines

  摘要：

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.

  DOI：

  10.1007/s007060200071
• 作为产物：
  描述：

  rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester 在 palladium on activated charcoal 硝酸铵 、 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟甲磺酸 、 氢气 、 四丁基硫酸氢铵 、 二异丁基氢化铝 、 potassium carbonate 、 cerous nitrate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 、 二乙二醇 为溶剂， -72.0~160.0 ℃ 、8.5 MPa 条件下， 反应 96.25h， 生成 1-methyl-6-(1-methyl-2,3-dihydro-1H-indol-3-ylmethyl)-1,2,3,6-tetrahydropyridin-3-ol
  参考文献：
  名称：

  Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines

  摘要：

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.

  DOI：

  10.1007/s007060200071

文献信息

• Intramolecular Alkylation of Aromatic Compounds XXXVI [1]. Stereoselective Synthesis of C/D-cis-Configured Ergolines
  作者：Eberhard Reimann、Wolfgang Erdle、Eugen Hargasser、Hermann Lotter

  DOI：10.1007/s007060200071

  日期：2002.7

  The stereoselective synthesis of cis-ergoline is presented. Starting from rac-N-benzoyl tryptophan methyl ester, the key compound indolinylmethylpyridin-3-one was prepared via a seven-step reaction in good yield. Since its cyclization to the desired ergolinone failed, the key compound was reduced to yield the two diastereomeric pyridin-3-ols; only one of them cyclized in trifluoromethanesulfonic acid, affording cis-ergoline. Catalytic hydrogenation of the latter gave N,N'-dimethyldihydroergoline, the X-ray crystallography of which revealed both the correct structure and identical relative configurations at C-5a and C-6a (SS or RR). Hydroboration and subsequent perruthenate oxidation of the Delta(9)-ergoline provided access to the regioisomeric ergolinols and ergolinones.